


Dessert For Two

by BeepBeepTimeToFloat



Series: Pennywise One Shots [6]
Category: IT (2017), Pennywise the Dancing Clown - Fandom
Genre: Biting, Choking, Dominant Pennywise, F/M, He calls himself Daddy, Oral Sex, Orgasm Denial, Possessive Pennywise, Public Sex, Rough Sex, Teasing, Vaginal Fingering, fucking against a wall
Language: English
Status: Completed
Published: 2017-11-21
Updated: 2017-11-21
Packaged: 2019-02-04 23:33:19
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,142
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/12782037
Author URL: https://archiveofourown.org/users/BeepBeepTimeToFloat/pseuds/BeepBeepTimeToFloat
Summary: Pennywise isn't happy when his S/O is invited on a double date, and comes along to make sure she remembers she's his.





	Dessert For Two

**Author's Note:**

> Inspired by a post by @tiltheweedstakeyou and @tasteslikebuttercream talking about Pennywise teasing his human while out to dinner.

Pennywise planted himself between her and the door, arms folded and a scowl on his face. The little shit was even pouting. She stared at him with exasperation, done with his tireless harassment.

“You’re mine. Why are you going out with someone else?” he asked, dangerously close to growling at her. She watched the red rims begin to appear around his irises before he caught it, reeling himself back in. 

“It’s not like I want to go,” she sighed, “Alex and her boyfriend are old friends. They’re…worried, because I haven’t seen them in ages. They think there’s something wrong.”

“You’re not answering my question, pet,” he fought a snarl, “Why do you have to go with another male?”

“Because they wanted to go on a double date, Penny! God, it’s not like I’m going to run off with him. I don’t even know the guy,” she argued. His eyes flashed from orange to red and then back again. 

“Tell them you don’t need a double date because you have me,” he responded, making her scoff and laugh. 

“Yeah, that’ll go over really well. ‘Sorry I haven’t seen you in months guys, but I don’t need a date because I’ve been fucking an interdimensional, child-eating clown’. Then they’ll really lock me up,” she shook her head and grabbed her keys, pinching the bridge of her nose. The sound of a car pulling up outside signaled that they were there. A horn honked and she glared at him, waiting for him to step aside. 

“I’ll be watching,” he growled, and she leaned up on her toes to kiss his bottom lip.

“I wouldn’t have it any other way,” she smiled, squeezing past him and going out onto her porch. She locked the door behind her and walked carefully along the stone path, nearly tripping in the heels she was wearing. When Alex called to set up the date, she’d heard the worry in her voice, and she had every right to be worried. In the months since Pennywise had come into her life, she’d been consumed with work and giving him every minute of her free time. Truthfully, she was just a little bit excited to have a night out, even if she had to deal with some poor guy trying to win her affections, blissfully unaware of the fat cock she’d be sucking before the evening was over. 

She slipped into the backseat beside her mystery man, smiling politely. 

“Hey guys! Sorry, I couldn’t find my keys,” she said.

“No problem! This is Jack,” Alex said, motioning to the man sharing the backseat. She looked over at him again, taking in his appearance. He was handsome enough; tall looking,   
dark hair and blue eyes with a genuine smile. Poor guy. 

“Nice to meet you,” he smiled, “Alex has told me a lot.”

“Oh boy, I’m in trouble now,” she laughed half-heartedly. 

 

The ride to the restaurant was okay, if not just the slightest bit awkward. Jack chatted her up, asking her about every aspect of her life. Alex would peek back at her, wiggling her brows expectantly. She’d shoot her a look that said ‘Shut the fuck up’ and go back to pretending like she was listening to how law school was going for him. One thing bugged her, though; the hairs on the back of her neck kept prickling, like someone was running their fingers along her skin. She felt it on her waist and legs, traveling right up to the hem of her dress. Swallowing hard, she scratched her skin, hoping it was just an itch. A quiet chuckle in her ear set her nerves on edge as Alex’s boyfriend parked the car and they all got out. 

Jack held the door for her, letting her go first as they walked and placing a hand on her lower back. She felt a gust of hot air on her cheek, knowing that Pennywise wasn’t happy. 

“Ah, shit!” Jack whispered under his breath, pulling his hand away. She looked over at him, staring down at his hand to see two tiny teeth marks. 

“Are you alright?” she asked, eyes wide. He lowered his hand out of her sight and put on a brave face.

“Yeah, I’m good, just a cramp,” he said, pulling the chair out for her to sit down when they got to the table. Once they were all seated, the waiter came over with a bottle of wine. 

She sipped from her glass slowly, feeling a knot in her stomach. Obviously Pennywise was watching, but he was making her nervous. Normally she didn’t mind his presence in the background, but tonight anxiety churched in her gut. 

The waiter hadn’t even come for their order yet when she felt it. Two gloved hands sliding gently up her calves, making goosebumps rise on the flesh. Her throat felt thick as she struggled to remember what it was that Jack had asked her.

“I…uh, I’m uh, I just finished up school,” she said shutting her eyes to think and snapping them open when the gloved hands rested on her kneecaps, gripping them tightly. She cleared her throat and leaned forward to rest her elbows on the table, discreetly kicking her foot up in an attempt to get Pennywise to fuck off.

“Ow! What the hell?” Alex asked, leaning down to rub her leg. Her eyes widened and her face went red.

“Oh my god! I’m so sorry! I didn’t mean to kick you,” she rambled, trying to explain herself. Alex gave her a strange look but let it go, turning back to talk to her boyfriend. She heard a chuckle from beneath the table and felt the hands grab her knees again. 

“Mm, my little pet on her first date with a human,” Pennywise’s deep voice drifted up and she clenched her jaw.

“It’s not my first date,” she grumbled under her breath, jerking her knee away from his hand, but he was strong and held on. 

“I’m sorry?” Jack asked, making her bring her attention back to him.

“Uh… I said it’s my fault I was late,” she wracked her brain for an excuse, “I just, uh, I always lose my keys.”

“Oh…well, don’t worry about it. We were only in the driveway for a few minutes,” he said, trying to comfort her. Pennywise laughed again and moved his hands from her knees up her thighs, pushing her dress high up into her lap. She peeked down and actually saw the white gloves, the thumbs digging into her inner thighs. His orange eyes had an evil glint in them as he looked up at her, and she watched him lick his lips. She tried to close her legs, shut him out completely, but he squeezed her flesh until it hurt and made her open back up. 

“…don’t you think so?” someone asked, and she looked up to see them all staring at her waiting for an answer.

“Uh, I guess,” she mumbled, trying to ignore what was going on beneath the table. Her hands were trembling, and she prayed nobody noticed them. Pennywise had her legs spread wide, a single finger tracing the slit that was concealed by her underwear. 

“Pay attention, pet. You don’t want to miss the conversation,” he scolded, rubbing his thumb against her clit teasingly. She stifled a gasp and balled her hand into a fist, gripping the cloth napkin in front of her. 

“So, Jack, what is it that you want to do after law school?” she asked, smiling even though tiny beads of sweat were breaking out on her forehead. 

“Well, I’m hoping to…” he started speaking, but she missed the rest of what he said. A cold nose pressed against her sex, inhaling and groaning. He backed off and slipped a finger beneath her underwear, gently touching her folds.

“So wet for Daddy,” he commented, chuckling and running his thumbs down the sides of her pink lips, only giving her an inch of pleasure. She tried to keep her breathing even and move away from the prying fingers, but she had nowhere to go. 

“He’s thinking about it, you know,” Pennywise spoke again, “About how badly he wants to fuck you. From what I can tell, he’s not very good at it.”

She bit her lip to keep from laughing, looking over at the brunette whose eyes kept glancing at her. Pennywise’s fingers trailed up past her pussy to her waist, taking hold of the underwear and slipping it off. Her eyes bugged from her head and she looked down at him, mentally pleading for him not to start what he was already dead set on doing. He slipped a single finger inside of her, using his thumb to softly rub her clit. Little shockwaves of pleasure washed over her and she sighed audibly.

“Hey!” Alex waved her hand in front of her face, “You gonna order or not?”

Panic made her freeze up, her eyes looking down at the menu in front of her, searching for something to tell the waiter who was glaring at her. 

“Uh, I’ll take the chicken,” she spit out, folding the menu with her shaking hands and practically throwing it at him. He arched a brow and walked off, leaving them alone.

“Are you alright?” Alex asked, “You don’t look so good.”

“Me? Oh, I’m fine!” she laughed with a strained smile as Pennywise’s finger pushed further in, rubbing her walls enough to get her soaked, but nowhere near ready to cum. That was exactly where he wanted her. 

“You sure you’re alright little one? You’re a little tense,” Pennywise said, slipping a second finger into her pussy and pumping it. Her fingers gripped the edge of the table and she shut her eyes, exhaling through her nose. He moaned, and she clenched around him. She loved it when he moaned, because it was so rare that he was reduced to vocalizing his pleasure. Her hips rocked into his touch and she spread her legs wider.

“What a dirty girl. What would your date say if he knew how Daddy was playing with your pussy under the table?” Pennywise continued, biting at her inner thigh. 

“Ah!” she squeaked, gaining the attention of the three individuals sitting with her, who stared in confusion.

“Sorry, I’ve been…having some problems with my knees. I just get shooting pains at random times,” the lies rolled off her tongue almost faster than she could think them up. 

“Your knees are going to hurt a lot more before I’m done with you, pet,” Pennywise said as he licked at where he bit her. His tongue traveled up, moving closer and closer to her juncture until he was almost touching it. He stopped though, letting her hang on in agony while he pretended to decide what to do to her next. She could feel herself moving towards her orgasm at an alarming rate; Pennywise’s fingers mixed with the fact that they were in a fucking restaurant with people less than a foot away worked her up so bad that she was sure they could hear the wet noises of his fingers stroking her walls. 

“You’re food is going to get cold if you stare at it any longer,” Alex commented as she twirled her pasta around her fork, not even looking up. She looked down, seeing the plate of chicken-something in front of her that seemed to appear out of nowhere, and tried to eat. Any time she opened her mouth to take a bite, Pennywise would rub her clit faster in an attempt to get her to make some obscene noise, but she managed to keep it together as best she could. It was obvious he was getting irritated at her, and as the waiter took their dessert orders, he dug his claws into her thighs to spread them yet again. 

“Pennywise gets something sweet, too,” he rumbled, latching his mouth onto her pussy. She nearly spit out the last sip of wine she was drinking, coughing and sputtering as he worked his tongue over her tortured bundle of nerves. He was slurping and moaning as he did it, turning her face a bright red from embarrassment. His tongue jutted into her slick entrance, writhing and hitting the one spot he knew could make her cum almost instantly. 

“F-Fuck,” she stammered, shutting her eyes and covering her face with her hands.

“What’s the matter?” Jack asked, making her jump.

“…Huh? Wha—Shit, sorry, um… I forgot that I have family…” her voice trailed off as Pennywise hummed, pulling his tongue out of her pussy and replacing it with two fingers. He wrapped his lips around her clit and sucked, spit and slick pooling in the chair she sat on.

“Family…?” Jack asked, waiting for her to finish her sentence. Pennywise pushed a third finger inside and her eyes fluttered shut, mouth nearly falling open as she felt her walls contract around him.

“Coming!” she half-shouted, “Family coming! To visit!”

Pennywise laughed against her aching pussy, but removed himself completely before she actually finished. She glanced down into her lap and saw that everything was back to normal, her dress where it should be, the puddle in her chair disappeared. The only reminder that the whole thing hadn’t been a liquor-induced hallucination was the fact that her panties were still gone, and her entire body was burning up.

“Oh…how nice,” Jack forced out, and she nodded quickly.

“Yeah, yeah, great. I’m gonna, uh, I’m gonna go get some air real quick,” she said, standing up and almost falling back down into her chair from the weakness in her legs. Before anyone could stop her, she was scurrying off towards the bathrooms, aimed for the emergency exit door at the end of the corridor. Outside, the air was cold on her flushed face and she leaned her back against the brick wall of the alley she found herself in. 

“Mm, my tasty little girl,” Pennywise’s mouth was right near her ear as he materialized, “So sweet for Daddy. Poor Jack could never make you feel that good with his tongue, huh, Princess?”

She clenched her jaw and growled angrily at him, taking hold of his collar to pull his face to her level. He stared at her, just the slightest bit surprised by her boldness, but pushed into her when he felt her lips on his. She bit his bottom one, drawing blood and his angry eyes were met with ones that were just as furious.

“Finish what you fucking started, clown,” she gritted her teeth together and he smirked, grabbing her by the back of her legs. He hoisted her up higher on the wall as she linked her ankles around his waist, using a claw to tear open his costume and free the erection he’d had since she sat down. It pushed against her already soaked core and he teased her with the tip, still not satisfied with how wound up she was. 

“Tell Daddy how much you want it,” he rasped, biting her neck and sucking the flesh.

“Goddamn it, Pennywise,” she whined, worn out from his incessant teasing. Her head pounded to the beat that her pussy throbbed.

“Speak up, little one,” he ordered as he grabbed her neck, squeezing.

“Please, Pennywise, I want you to fuck me so bad,” she gave in. He laughed and bucked his hips up, sliding into her pussy with ease. She gasped, desperate for that full feeling to never go away as she rocked her hips into his thrusts. He was panting into the crook of her neck, bouncing her on his cock, every snap of his hips going faster than the last. 

“So tight and wet,” he grunted, “Such a good girl for Pennywise, taking my cock.”

She moaned, head banging into the brick wall; his words alone made her want to cum, and the steady movement of his hips set her on a course for a mind-numbing orgasm. Her fingers gripped his shoulders, nails tearing little holes in the silk. Pennywise watched from the corner of his eye as her breasts bounced with each thrust, making his mouth water and his cock twitch. 

“Cum for Pennywise,” his voice was deepening, the true form straining against the clown’s, “Nice and loud so your date can hear who you belong to.”

He unwound one arm from her waist and slipped it between their bodies, rubbing her clit until she was gasping for air.

“Oh, fuck, Penny!” she shouted, pussy clenching around his cock as she came. He stuck two fingers into her mouth, quieting her down as he fucked her through it and got ready for his own end. She sucked on them, earning an appreciative bite from him. Deep growls and incoherent sentences erupted from his mouth as he pounded against her hips until he pushed in deep, filling her to the brim with his hot seed. His hips bucked every so often, pumping her full as he leaned his forehead against the wall, panting. She could feel it dripping down her thighs and he released her, steadying her on her feet. The two of them caught their breath and she smiled weakly at him.

“Take me home,” she said, straightening out her dress and smoothing down her hair.

“Now, now. You can’t just leave without saying goodbye,” he wagged a finger in front of her, “Go tell them you’re leaving and then we’ll go.”

She rolled her eyes but went inside anyway, stopping in the bathroom to clean herself off as best as she could. There wasn’t much she was able to fix; her makeup was smeared, her hair looked like a bird’s nest, bites and fingers prints peppered her neck. Still, she made her way back to the table and grabbed her purse, giving the three of them an apologetic look.

“Hey, I hate to eat and run, but there’s something I’ve got to take care of,” she said, glancing over at the bar and feeling her jaw drop.

A very tall, very human Pennywise stood with his hands in the pockets of his expensive suit, blue eyes trained on her. They all followed her gaze and saw the man, who winked and beckoned her with his pointer finger. She looked back at them and was going to explain, but couldn’t bring herself to come up with one more lie that evening. Instead, she walked off towards the stranger; he snaked an arm around her waist and let his hand fall to her ass, squeezing it while he looked over his shoulder at the man at the table whose jaw hit the floor. 

“You ready for round two, Princess?” he asked, licking his full lips and staring down at her. 

“Always,” she grinned, taking his hand as they left.


End file.
